Facilitating Challenging Discussions: Tools for Constructive Conversations

In today’s complex and polarized environments, the ability to facilitate challenging discussions is a critical skill for leaders, educators, and community members alike. These highly interactive workshops offer practical tools and strategies for creating spaces where constructive dialogue can thrive—even when the topics are difficult or emotions run high.

Participants will learn how to:

• Set the tone for respectful, inclusive, and productive conversations

• Navigate common group dynamics that can derail discussions

• Recognize and manage their own emotional reactions in the moment

• Support others in engaging thoughtfully and authentically

Through real-world scenarios, role plays, and reflective practice, you'll leave with increased confidence and concrete techniques to guide meaningful conversations in your work and community. Learn and practice key skills for leading conversations with confidence and care. Ideal for anyone who leads or participates in conversations on complex or sensitive topics.

This is a LIVE Workshop!

Be prepared to have your camera on and fully participate and practice in a supportive environment! We learn and improve by doing. New and experienced facilitators welcome.

Sessions will not be recorded to allow people to engage freely. Resources will be shared.

4-part series: Best to attend them all since they will build on each other but can attend individual sessions.

Fridays: Oct. 24, Nov. 7, Nov. 21, Dec. 5, 2025 12:30-3:30pm ET

This workshop series is offered on a sliding scale pricing model to increase accessibility for all. Each session is priced on a sliding scale of $25-$100. No one will be turned away for lack of funds. If needed, please contact us directly to prepare alternate payment arrangements.

Session 1 Oct. 24: Essential Skills

• Creating the container
• Fundamental skills (e.g. listening, reflecting, asking questions, summarizing, managing participation)

Session 2 Nov. 7: Facilitating Conflict/Differences in Viewpoints

• Approaches to conflict
• Strategies for making conflict/differences constructive

Session 3 Nov. 21: Attending to Social Identities and Power Dynamics

• Common patterns between dominant and marginalized groups
• Addressing microaggressions/biased comments

Session 4 Dec. 5: Managing Ourselves: How to keep our s*** together

• Understanding our biases and triggers/activations
• Tools for self-regulation and emotional balance

About Dr. Diane Goodman:

Diane J. Goodman, Ed.D. (she/her) has over 40 years of experience as a facilitator and educator with a wide range of groups and organizations. Through her training and consulting, she helps people develop the capacity to create environments where everyone can thrive.

She is the author of Promoting Diversity and Social Justice: Educating People from Privileged Groups (2000/2011) and co-editor and contributor to Teaching for Diversity and Social Justice (3rd and 4th ed. 2016/2022), as well as many other publications. You can learn about her and her work as well as subscribe to updates at www.dianegoodman.com